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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 10, pp 903–912 | Cite as

Cycloaddition of [3]dendralene derivatives to dinitrobenzofuroxan and nitrobenzodifuroxan

  • Pavel G. MorozovEmail author
  • Sergey V. Kurbatov
  • Yulia P. Semenyuk
  • Oleg N. Burov
  • Mikhail E. Kletskii
  • Nikita S. Fedik
  • Konstantin F. Suzdalev
Article

Abstract

It has been shown experimentally (by NMR spectroscopy and X-ray structural analysis) and theoretically (by quantum-chemical calculations according to DFT with B3LYP/6-31G* basis set) that the cycloaddition of [3]dendralene derivatives to nitrobenzodifuroxan and dinitrobenzofuroxan occurs by a stepwise mechanism with a σ-complex as intermediate. It was shown that the cycloaddition steps occurring contrary to the Alder endo rule are characterized by significant global electrophilicity index differences for the reagents (Δω > 3.0 eV). The stages with Δω ≤ 3.0 eV occurred in accordance with the Alder endo rule as concerted processes. X-ray structural analysis and quantum-chemical calculations within the framework of AIM model identified intramolecular attraction forces between non-bonded atoms in the cycloadduct of phenyldendralene and nitrobenzodifuroxan.

Keywords

dendralene dinitrobenzofuroxan nitrobenzodifuroxan cascade cycloaddition Diels–Alder reaction 

Notes

This study was supported by a Russian Scietific Fund grant (project 14-13-00103).

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Pavel G. Morozov
    • 1
    Email author
  • Sergey V. Kurbatov
    • 1
  • Yulia P. Semenyuk
    • 1
  • Oleg N. Burov
    • 1
  • Mikhail E. Kletskii
    • 1
  • Nikita S. Fedik
    • 1
  • Konstantin F. Suzdalev
    • 1
  1. 1.Southern Federal UniversityRostov-on-DonRussia

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